Startup Hustle
by Startup Hustle
Startup Hustle is a podcast for entrepreneurs, by entrepreneurs. With the mission of telling the real story of startups and entrepreneurs, topics range from funding to failure and beyond. If you want to start, own, or build a business then you're in the right place.
Episodes
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Building the Ramp of the Philippines: Fintech for the Underbanked
"There are eight digital banks trying to build the Chime of the Philippines. No one's building the Ramp or the Brex. That's the opportunity." I talked with Zach Marks, founder and CEO of Jia, on Startup Hustle this week. Jia is building modern digital banking for small businesses in emerging...
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Nothing to Lose: What Really Drives Entrepreneurs
"There's no magical growth lever. You just do a good job, every day, for 23 years, and the referrals do the rest." I talked with Matt Watts, founder of MWA Projects and author of Made With Ambition, on Startup Hustle this week. Matt designs and builds some of the most striking commercial spaces…
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The 2026 State of IT Staffing: Trends in Hiring, AI, and Offshore
"Both things are true. Software jobs are projected to grow 15%, and 74% of employers say they can't fill the roles. That's the whole story of IT staffing in 2026." This week on Startup Hustle, Matt Brown, Full Scale's head of marketing, put me in the guest chair to walk through our new State of…
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Why AI Made Software Engineers More Human
"AI scribes are just a feature. The record of clinical judgment is the moat." I talked with Kush Shah, founder and CEO of Noted Dent, on Startup Hustle this week. Noted Dent uses AI to handle clinical documentation for dentists, so practitioners aren't stuck writing notes at 11pm or on the…
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LeadershipOS Decoded: Building Teams That Run Without You in the Room
"Back in the 1900s when I was crossing the Great Plains in a covered wagon, programming in the back, the cover headline was: Software Development is Dead." I talked with Anthony Jackson, a CTO with 30 years across healthcare tech and enterprise software and author of the Architecture Protocol...
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It's Not About the Code. It's About the Problem.
I don't view engineers being out of a job. I view software engineers finally coming back to a real job." I talked with Adrian Gutierrez, co-founder of Ledgre, on Startup Hustle this week. Ledgre is an AI-native accounting platform built specifically for real estate investors, putting agentic AI…
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The Speed of Context: Why AI Changed What Engineers Actually Do
Most engineering teams are still optimizing for the wrong thing. They chase the speed of code when the real bottleneck is the speed of context. Matt Watson and Eban Bisong, founder and CEO of Senvi, get into what actually changes when AI moves from a coding tool to a teammate. Eban has spent his...
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AI, Protein, and GLP-1s: What's Actually Working in Health Tech
Most people are already asking AI about their health. Almost none of them believe the answers. Around 40% use it to make wellness choices, but fewer than 5% trust what it says. Matt Watson and Josh Anthony, CEO of Nlumn, dig into why. Josh has spent 25 years in food and nutrition, and his take is...
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Building Software Solo with Beth Epperson of Legacy Purposed
Matt Watson sits down with Beth Epperson, founder and CEO of Legacy Purposed, here in the Kansas City area. Beth came up through marketing and branding, including the brand launch for Hyvee Arena, before deciding to build something of her own. Her company is built around two products. Aligned...
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Geothermal Energy and the Future of Data Center Power
Data centers are multiplying fast, and the energy demands are staggering. Matt Watson sits down with Tim Tarver, founder and CEO of Exceed Geo Energy, to talk about one of the most underrated power sources in the conversation: geothermal. Tim breaks down how his company is adapting drilling...
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From Excel Sheet to 13,000 Customers: How Sean Tepper Built Tykr
Most retail investors don't know what to do after they open a brokerage account. Sean Tepper was one of them until he built a traffic light rating system for stocks and turned it into a SaaS platform used by 13,000 customers across 50 countries. In this episode of Startup Hustle, Matt Watson sits...
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Eric Ries: Why Good Companies Go Bad
Eric Ries wrote The Lean Startup. Sold 2 million copies. Helped hundreds of people build companies from nothing. Now he's back with a harder question: why do so many of those companies eventually go bad? In this episode, Matt Watson sits down with Eric to talk about his new book Incorruptible—a...
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The Non-Technical Founder Who Beat the Developers
Most founders get the order wrong. They build for two years, then ask a marketer how to sell it. Connie Lund flipped the script. She started Zaboom with no dev team, no code background, and no VC funding. What she had was 50+ years of combined marketing and product experience, a GoHighLevel...
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Stop Hiding Behind Process (You Should Own the Product Instead)
Most product managers are just project managers with a fancier title. They make zero real decisions, answer to everyone, and wonder why nothing ships on time. Willis Jackson has been building product teams for over a decade. He's blacklisted entire companies from his hiring pool. And he moved to...
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The Secret to Winning Venture Capital: What 2,000 Startup Investments Taught Dave Lambert
Most founders think investors bet on ideas. They don't. Dave Lambert has funded over 2,000 companies through RightSide Capital, and he's seen this pattern play out thousands of times. Great product. No revenue traction. Wrong ask, wrong timing. Automatic no. In this episode of Startup Hustle…
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Are Software Engineers Really at Risk? Mohan Reddy Weighs In
Matt Watson sits down with Mohan Reddy, serial entrepreneur and Chief Scientist at Cornerstone AI Labs, to explore how AI is fundamentally reshaping the way we think about work, skills, and human potential. Mohan shares the origin story of Skyhive—a workforce intelligence platform built to…
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How AI Is Disrupting Education with Katie Boody Adorno of LeanLab Education
AI is changing how kids learn. But are schools ready? Katie Boody Adorno is the founder and CEO of LeanLab Education. She's spent 13 years trying to close the opportunity gap in public education. In this episode, she and Matt break down how COVID widened learning disparities, why high-dosage...
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AI Isn't Killing Software Jobs: It's Changing Who Builds What
Zach Klempf is back! He joined Matt Watson on one of the early episodes of the show. Now, Zach is president of AutoManager, a private equity group with five automotive software companies under its umbrella. In this episode, Zach and Matt get into how AI is making senior engineers more productive....
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From Personal Tragedy to Healthcare Innovation
In this episode, entrepreneur Chris Jones shares his journey from personal tragedy to building MatchRite Care, a healthcare data integration platform. He discusses product-market fit, scaling strategies, and the importance of community and continuous learning in entrepreneurship. ⏱️ Episode...
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Matt & Mark Roberge
In this episode of Startup Hustle, Matt Watson interviews Mark Roberge, a former HubSpot executive and current venture capitalist, about his journey from engineering to sales and the importance of scaling startups. Mark discusses the genesis of HubSpot, the significance of sales in startups, and...
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Revolutionizing Hiring with GitHired
In this episode of Startup Hustle, Matt Watson interviews Krishna Oza, founder and COO of Git Hired, discussing the challenges of hiring software engineers, particularly for startups. Krishna shares his personal experiences that led to the creation of GitHired, an AI-driven platform designed to...
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Harnessing AI for Business Success
In this episode of Startup Hustle, Matt Watson interviews John Morlan, founder and CEO of Smarter Risk, about the transformative impact of AI on startups. John shares his journey of integrating AI into his business, enhancing productivity, and improving collaboration with developers. He discusses...
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Navigating Entrepreneurship: Insights from Matt Haycox
In this episode, Matt Watson interviews Matt Haycox, an experienced entrepreneur who shares insights from his 25 years in business, focusing on capital raising, the challenges of entering the tech space as a non-technical leader, and the impact of AI on business development. Haycox discusses his...
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Creative Engineering at Scale What Big Companies Get Wrong and Right with David Mitchell
What happens when you mix creative agency chaos with world-class engineering? You get teams that don’t just write code—they own the product. In this episode, I’m talking with David Mitchell, CTO at VML, one of the biggest creative agencies on the planet. With thousands of engineers and global...
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Engineering Clarity in the Age of AI with Seth Rosenbauer
Engineering Clarity in the Age of AI: How Docs, Context, and Product Thinking Shape Better Software Seth Rosenbauer is the founder of a tool that uses AI to help engineers create better documentation—and, more importantly, the right thing, faster. But this conversation isn’t just about tooling....
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Fixing the Language Barrier Between Engineers and Executives with Karell Ste Marie of The Serious CT
Matt is joined by Karell Ste-Marie, founder of The Serious CTO YouTube channel. Together, they tackle one of the biggest hidden challenges in software companies: the language and cultural barrier between engineers and executives. Karell and Matt break down why innovation is so rare in large...
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Prompt Prototyping, AI Vibes, and the New Rules of Product Management
Product management is being rewritten in real time, and AI is doing the editing. Matt sits down with Jerel Velarde, product manager at Full Scale Ventures, to discuss how AI is reshaping the relationship between PMs and engineering. We dive into what Jerel calls prompt prototyping, how…
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Why Teams Lose Their Way at Scale with Randy Silver
Matt is joined by product and leadership consultant Randy Silver to unpack one of the most frustrating problems in product organizations: everyone knows where they want to go, but no one knows how to actually get there. Together they explore what causes this breakdown in execution, how companies...
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How AI Is Really Impacting Developer Experience and the Real Productivity Problem with Laura Tacho
In this episode, Matt is joined by Laura Tacho, CTO at DX — one of the leading voices in developer experience research and tooling. Together, they unpack how AI is really affecting software development teams, why developer experience has a “marketing problem,” and why organizational friction —…
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Why We Still Need Software Engineers in the Age of AI with Brian Jenney
AI can scaffold an app in seconds, but can it refactor that thousand-line React file when the first bug hits production? In this episode, I sit down with Brian Jenney software engineer and program owner of the coding bootcamp Parsity, to draw a hard line between “code that runs” and “code that...
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Simple Systems that Let CTOs Delegate Ownership—and Still Sleep at Night with Brittany Rastsmith
If you’re running a startup, chances are you’re the bottleneck. Brittany Rastsmith joins Product Driven to talk through why founders constantly end up in this trap and how to escape it. She works with early-stage companies through her consulting firm, Bloom Remote, and she's seen it all. We get...
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Technical Co-Founders are Startup Gold with Noah Lindner
The 10X Developer Decoded: Why Technical Co-Founders Are Startup Gold 💎 In this revealing conversation, we unpack one of tech's most polarizing concepts while exploring the brutal realities of building technical partnerships in today's startup ecosystem. Host Matt Watson and Noah Lindner...
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CTO Levels and the Path to Strategic Tech Leadership with Kathy Keating
From Coding to Catalyst: The Evolution of Technology Leadership 🚀 Journey through the transformation of modern CTOs with industry veteran Kathy Keating, who shares battle-tested insights from scaling teams of 2 to 450+ engineers. This episode unravels the complex tapestry of technology…
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Inside 'Product Driven': Why This New Book is Every Engineering Leader's Must-Read
Product Driven: Building Software Teams That Ship Value 🚀 In this special book launch episode, we dive deep into the intersection of engineering leadership, product thinking, and the transformative impact of AI on software development. Join Matt Watson and Craig Ferril as they explore the...
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The Engineering Leadership Book That Actually Shows You How to Build Product-Minded Teams
Product Driven: The Book Launch - A Software Leader's Journey to Creating High-Performance Teams 📚 After months of intensive writing and years of industry experience, Matt Watson unveils his groundbreaking book "Product Driven" - a comprehensive guide for engineering leaders seeking to build…
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Rethinking Requirements When Engineers Are No Longer the Bottleneck with Chris Rickard
Breaking Through Requirements Hell: How AI is Revolutionizing Software Development 🚀 In this compelling exploration of technological transformation, host Matt Watson connects with Chris Rickard, founder of UserDoc, broadcasting from Vietnam. Their conversation unveils a profound shift happening...
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How Boddle's Product-Driven Approach Built Educational Games That Kids Ask Parents to Buy with Clarence Tan
Learning Through Play: How Boddle Built Educational Games That Kids Actually Want In this insightful conversation, Matt Watson talks with Clarence Tan, founder and CEO of Boddle Learning, about their journey building educational games that have reached over 10 million users. Clarence shares how...
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How Feedback Loops Transform Development Efficiency with Ashley Davis
Feedback-Driven Development: Optimizing Your Software Engineering Process In this enlightening conversation with author Ashley Davis, Matt Watson explores the concept of feedback-driven development and how it shapes effective software engineering practices. Ashley, author of "Bootstrapping...
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Product-Led Growth vs. VC Funding: Lessons from 25 Bootstrapped Startups with John Rush
Bootstrapping vs VC: John Rush on Building 25 Successful Products 🚀 In this enlightening episode of Product Driven, host Matt Watson sits down with serial tech entrepreneur John Rush. Known for his prominent presence on social media platforms like Twitter (X) and LinkedIn, John shares his…
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AI Adoption Strategies: Inspiring Developer Teams to Embrace Intelligent Tools with Senad Santic
AI and Agency Evolution: Navigating the Future of Software Development 🚀 In this thought-provoking episode of Product Driven, Matt Watson welcomes Senad Santic, owner of Zendev software development agency and founder of LinkBound. They dive deep into how AI is reshaping software development...
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Three Core Principles CTOs Use to Create an Engineering Culture that Inspires and Retains Top Talent with John Durrant
Building Human-Centric Engineering Teams: Culture, Motivation, & Purpose 🛠️ In this episode of Product Driven, Matt Watson talks with John Durant, founder of Human Centric Engineering, about the critical elements that create high-performing engineering cultures. John explains how mastery,...
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AI in QA Testing: How TestChimp is Revolutionizing Software Quality Assurance with Nuwan Samarasekera
🧪 The AI Testing Revolution: Reimagining QA in the Era of Generative Intelligence In this intellectually stimulating conversation, Matt Watson and Nuwan Samarasekera (Founder & CEO of TestChimp) explore the transformative impact of generative AI on software testing methodologies. As AI…
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Solving the Hidden Challenges of Growing Engineering Teams at Scale with Gleb Braverman from HackerPulse
🔍 Engineering Visibility: Unlocking Team Performance at Scale with Hacker Pulse In this intellectually stimulating exploration, Matt Watson and Gleb Braverman (Founder & CEO of Hacker Pulse) delve into the universal challenges that emerge when engineering organizations reach critical mass. From...
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How Full Scale Ventures Builds Product-Driven Startups with Craig Ferril
Full Scale Ventures Launches & The Power of Venture Studios 🚀 In this transformative episode of Product Driven, host Matt Watson introduces his exciting new venture with Craig Ferril—Full Scale Ventures. They dive deep into the concept of venture studios, exploring various models and explaining...
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When Great CTOs Go Into Beast Mode with Ron Timoshenko
🦸♂️ Unlocking CTO Mode: When Technical Leaders Become Innovation Heroes In this intellectually stimulating conversation, Matt Watson and Ron Timoshenko (CIO of Rimbull Health) unpack the multifaceted nature of the CTO role and explore the critical moments when technical leaders must activate...
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The Best Startup Pitch Framework
In this episode, Matt Watson interviews Rajiv Nathan, the Startup Hype Man, who shares insights on how to pitch a startup to investors and customers effectively. Rajiv discusses his journey from a marketing background to becoming a pitch expert, emphasizing the importance of understanding the…
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Targeting the Midmarket, Growing with SEO
In this episode, Matt Watson interviews Ben Taylor, founder and CEO of Soft Ledger, about his journey in creating accounting software. They discuss the challenges of building a product in a competitive market, the importance of identifying gaps in existing solutions, and the lessons learned from...
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Starting vs Growing a Business
In this episode, Matt Watson and Sean Beckner discuss the journey of entrepreneurship, investment strategies, and the evolution of business growth. Sean shares his experiences transitioning from a startup founder to an investor, highlighting the importance of timing in business exits and the...
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Boutique VCs & The Effect of AI
In this episode, Matt Watson speaks with Joseph Ruscio, a partner at Heavybit, a venture capital firm focused on investing in software development-related companies. They discuss the evolving landscape of venture capital, the unique value niche VC firms provide, and the impact of AI on software...
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Scaling with Affordable Talent from the Philippines
In this episode, Matt Watson and Yoni Kozminski discuss the intricacies of hiring talent in the Philippines, exploring Yoni's journey from creative advertising to building a recruitment agency. They delve into the challenges of scaling a business, the importance of value creation in sales, and…
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About this show
Startup Hustle is a podcast for entrepreneurs, by entrepreneurs. With the mission of telling the real story of startups and entrepreneurs, topics range from funding to failure and beyond. If you want to start, own, or build a business then you're in the right place.
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